Optimizing images for Help and Print/PDF

i'm struggling with how to optimize graphics so they look good in both Help and print/pdf output.
I use Snag-it to Capture and save as PNG 300 dpi.
I often put the images in Vision and add callouts and save as PNG.
From RH I generate a printed output (Word) which I convert to PDF.
So with all the programs an image goes through (snag-it > visio > RH > Word > PDF) i'm not always sure what the best settings are.
Does anyone have guidelines/suggestions  ?
Thanks

I've had very good luck going from a SnagIt capture to Robohelp to Word to PDF. I add callouts directly in SnagIt to save myself a step and save the files as a 24-bit (True Color) PNG. The graphics are very legible in the WebHelp output, in the Word document, and in the printed PDF.
The only thing that doesn't work well, I've found, is when I reduce the size of a graphic in either SnagIt or Robohelp. Instead, to keep a graphic's dimensions manageable, I either shrink the s/w application window before I grab the screen, capture just a portion of the screen, or crop the screen shot in SnagIt.
What problems have you been encountering?

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